title: Cyclic sulfoxides garlicnins B2, B3, B4, C2, and C3 from Allium sativum.
abstract: Several novel sulfides, called garlicnins B2 (1), B3 (2), B4 (3), C2 (4), and C3 (5), were isolated from acetone extracts of garlic, Allium sativum L. and characterized. These garlicnins are capable of suppressing M2 macrophage activation and they have a novel skeleton of cyclic sulfoxide. The structures of the former 3 and latter of 2 were deduced to be 2-(sulfenic acid)-5-(allyl)-3,4-dimethyltetrahydrothiophene-S-oxides and 2-(allyldithiine)-5-(propenylsulfoxide)-3,4-dimethyltetrahydrothiophene-S-oxides, respectively. The mechanism of the proposed production of these compounds is discussed. The identification of these novel sulfoxides from garlic accumulates a great deal of new chemistry in the Allium sulfide field, and future pharmacological investigations of these compounds will aid the development of natural, healthy foods and anti-cancer agents that may prevent or combat disease.
authors.affiliation: Faculty of Pharmaceutical Sciences, Sojo University, Kumamoto 860–0082, Japan. none@ph.sojo-u.ac.jp
authors.forename: Toshihiro
authors.initials: T
authors.lastname: Nohara
authors.forename: Yukio
authors.initials: Y
authors.lastname: Fujiwara
authors.forename: Tsuyoshi
authors.initials: T
authors.lastname: Ikeda
authors.forename: Kohtaro
authors.initials: K
authors.lastname: Murakami
authors.forename: Masateru
authors.initials: M
authors.lastname: Ono
authors.forename: Daisuke
authors.initials: D
authors.lastname: Nakano
authors.forename: Junei
authors.initials: J
authors.lastname: Kinjo
mesh_terms: D000096:Acetone / Q000737:chemistry; D000498:Allyl Compounds / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D015703:Antigens, CD / Q000378:metabolism; D015214:Antigens, Differentiation, Myelomonocytic / Q000378:metabolism; D002460:Cell Line; D004220:Disulfides / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D005737:Garlic / Q000737:chemistry*; D006801:Humans; D008264:Macrophages / Q000187:drug effects; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D011956:Receptors, Cell Surface / Q000378:metabolism; D013454:Sulfoxides / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D000098902:CD163 Antigen
chemical_list: D000498:Allyl Compounds; D015703:Antigens, CD; D015214:Antigens, Differentiation, Myelomonocytic; D000098902:CD163 Antigen; D004220:Disulfides; D011956:Receptors, Cell Surface; D013454:Sulfoxides; D000096:Acetone; C028009:diallyl disulfide